Generalist updates
Dec 30, 2022

December Mailbag

Answering readers' questions on venture capital fundraising, my favorite reads, information diets, and more.

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1. What tools and techniques do you use for deep research? – Ned, Australia

I’m easily intrigued by new research tools and note-taking platforms. Over the years, I’ve tried most. And yet, I still rely on Google Docs to compile information and turn it into usable text. For whatever reason, the simplicity and reliability of Docs make it hard to dislodge, even though there are fine-tuned alternatives for bookmarking, information organization, notes, and so forth. 

The tools that have succeeded in achieving regular usage and that I would miss if they disappeared are as follows:

  • Arc. An elegant next-generation browser. It takes a bit of getting used to, but once you master a few hotkeys and get used to the different UI, it becomes clear that this is a substantial step up from Google Chrome, Safari, Brave, and other challenger offerings I’ve tried in the past. 
  • Alfred. I’ve been using Alfred for years and swear by it. Perhaps because it is run by a small (probably highly profitable) business rather than a venture-backed firm, it doesn’t attract much attention, but it is an incredible assistant. I mostly use it for snippets, which I use as often as possible. 

A tool I haven’t used deeply enough to have a sophisticated opinion on yet (but seems promising) is Mem. I’ve tried it here and there, but the team appears to have rolled out new features over the past few months. I’d like to sit down with it at some point and thoroughly assess how I might use it and if it could improve my workflow.

The best thing I do to achieve a deep work state is enter what I call “bunker mode.” I turn my phone and computer to “Do Not Disturb,” block distracting websites (Twitter is blocked for me 99% of the time) and occasionally force myself into using a Pomodoro timer. Usually, I’ll listen to a bit of music to give me a boost, but pretty quickly, I switch it off for better focus. The AirPods do a good job of blocking external noise, and as long as the work is interesting, it's relatively straightforward to work intensely for several hours at a time. 

If I’m not feeling inspired, especially on the writing front, I’ll spend fifteen minutes reading quotes from authors I like. (I will search “Coetzee most beautiful quotes” and peruse Goodreads like a weirdo). Reading good, evocative writing activates a part of my brain that makes me want to work, create, think. Reading about good writing and good writers on LitHub often has a similar effect.

To ensure I don’t miss an appointment while in bunker mode, I tend to set alarms on my phone in advance. I’ll do this most mornings – take five minutes and set alarms that let me know I am about to switch, like a school bell. I picked this habit up from a friend and found it very useful. Not only does it ensure you won’t work through something important, it removes the cognitive stress that the possibility of missing an appointment creates. It feels unnatural at first not to check your calendar every thirty minutes, but this weans you off the habit. 

2. What is your information diet? – David, Colombia

I split my time between “hunting” and “foraging.” 

Researching a piece for The Generalist or assessing an investment for Generalist Capital is a form of hunting. I have a clear goal and a plan of attack. I have grounds I like to visit and tactics that yield decent results. Above all, my desire is to find the most-informationally rich sources as efficiently as possible. To do so, I visit places like Harvard Business Review (especially the case studies), Bloomberg, The Financial Times, TechCrunch, The Information, Axios, and many others.

Unlike hunting, foraging is done without a specific target in mind. I hope to find something valuable, but I don’t know what. It could be a new idea, a fresh opinion, a writing technique, a bit of wisdom, or something else. By and large, I try and spend my foraging time reading classic books, usually novels. Though there are exceptions, I am broadly skeptical of business books which tend to be twenty-page theses gavaged into four-hundred-page tomes. I’m also mindful that I don’t tend to encounter fiction as part of my day-to-day work – if I want to keep reading these works and benefiting from their wisdom, I must do so concertedly.

3. If you were to restart your journey, how would you seek out LPs without your current audience, and would you choose to raise a fund or spin up SPVs? I have angel invested in a few interesting companies and want to take my game to the next step. I’d appreciate any and all thoughts. – K Man

First, it's important to recognize that venture capital has several different buying profiles. In broad strokes, I would say there are four common LP motivations:

  1. The altruistic buyer. This LP believes in you and wants to help, however possible. They tend to be the first people in your fund and are often friends, family, old co-workers, and deeply-engaged supporters. Though having an audience grows this category, most people have some version of this. 
  2. The access buyer. This LP is investing in your fund to build a relationship with you or your portfolio. They might do this to create social capital (e.g., being able to say, “I’m an investor in Taylor Swift’s fund”) or to get a first look at your deals. Individuals, family offices, and other venture funds (or their GPs) can fit this category. Though the way this relationship is leveraged may differ, the fundamental desire to benefit from proximity is the same. 
  3. The educational buyer. This LP treats their investment as a form of tuition. They want to learn about tech, venture capital, or a sector you cover and believe this gives them an avenue to do so. High-net-worth individuals – often from older generations – fall into this category, as do professional investors looking to wrap their heads around emergent categories (e.g., crypto, biotech, AI). 
  4. The returns buyer. This LP wants you to turn their money into more money. They may care about many other things, too, but at the end of the day, they will consider the venture a success or failure based on the numbers you put on the board. Professional fund-of-fund investors mostly fall into this category. 

These are not perfectly discrete categories. Even the altruists would prefer you to make money for them, and those in search of returns may also want to leverage your position to front-run future rounds. Nevertheless, every LP usually has a clear leading motivation, even if it can take a little while to figure out. 

Pitching to each of these four personas is a very different experience. An argument that might work with one LP may be meaningless to another. If I were raising a fund without The Generalist’s audience, I would think hard about which personas would find me most appealing and why. 

Do I have an extensive network of moneyed well-wishers? Am I someone people see social or tactical value in building a connection with? Am I focused on a sector that few understand, but many want to? Do I have a track record? The answers I might provide to these questions would guide my fund size, strategy, and target LP base. 

For what it’s worth, the hardest persona to sell to as a new fund manager is number four. This also happens to be the category with the deepest pockets. Someone might invest hundreds of thousands or even a few million dollars because they’d like to build a relationship with you or want to learn from your expertise. But no one forks over tens of millions without the expectation of a return. Unless you’re coming from a well-known venture firm or have an extremely impressive track record as an angel, you’ll likely have limited luck with this group on a first fund, but it’s always worth a shot. Try to show your fund’s unique strengths and the best proxies for performance, such as a demonstrable ability to invest alongside elite funds or positive reviews from founders.

Should you run SPVs instead? There are certainly benefits. For one thing, it’s much more flexible. If you’re too busy or feel venture investing isn’t as fun as you’d hoped, you can stop anytime. There’s also a financial benefit. Rather than earning carry from the combined performance of a fund, SPV leads earn it on a deal-by-deal basis. This can make a big difference! 

A final upside is that you have a definitive product to sell to LPs. Instead of saying, please invest in this vehicle, I promise I will do good things, you get to say, invest in this amazing, tangible company. It’s a shift from the hypothetical to the real. 

There are, of course, downsides. By and large, SPVs get into deals last. That’s not always the case, but founders tend to want to work with a committed, intentional partner that can provide some discrete benefit. SPVs are an emergent collection of backers, and many leads don’t have a particular founder-focused offering. Those that do may be able to fight against the adverse selection that SPVs have to reckon with.

The other major drawback is that SPVs are a lot of work. They may require less consistent effort than a fund, but the lead has to go through a mini, time-boxed fundraising process whenever it's time to invest in a new deal. There are moving pieces, perhaps hundreds of stakeholders and a ticking clock. 

As you think through this next step, I’d ask yourself the following questions: 

  1. Do I want venture investing to be a continuing experiment or enduring practice?
  2. Would I prefer to endure the long, dispiriting slog of fundraising or an endless string of SPV fire drills? 
  3. Do I have a strategy that could appeal to at least one of the LP personas? 
  4. Do I have a strategy to access deals (and does this change depending on the structure I pick)?

There’s no correct answer, but thinking this through may help guide your decision. 

4. Do you drink coffee? If yes, how do you like your coffee? If no, what helps you get through long writing periods? – Koromone, Managing editor, TechCabal

Yes! I love coffee. Usually, I’ll have an iced cortado with almond milk. I probably drink too many of these, but they provide a reliable writing boost. 

5. You obviously read and have read a lot. I’d love to hear about your relationship with books: when and how it started, which books were catalysts for how you saw the world or thought differently, and your top ten lifetime reads. – Jonny, LA

From what I have heard, I was obsessed with books from the very beginning. As the story goes (beware some self-serving mythologizing), I would happily spend hours in my crib fumbling through fuzzy folios, absorbed by their contents. 

Many of my earliest memories involve reading. As a child, I worked my way through Roald Dahl (Matilda was the first book I read over 200 pages, a length which seemed incredible to me, a feat which made me intensely proud). My favorite of his stories was, as you might have guessed, Fantastic Mr. Fox, which I read several times over, even going so far as to time myself for some unknown reason. Other favorites included The Chronicles of Narnia, Ingri and Edgar D'Aulaire’s Book of Greek Myths, and the Just William series by Richmal Crompton. 

The last of these made a particularly strong impression on me – if you are a parent of young children, I cannot recommend it enough. Written in the early 1900s in England, Just William details the adventures of schoolboy William Brown and his impish friends. Though aimed at children, the caliber of writing is exceptional. The rhythm of the sentences is particularly elegant, and the stories themselves are charming, entertaining, worldly, and clever. 

It’s strange to say, but much of the way I write today can probably be traced back to reading Just William and listening to the audio cassettes each night as I fell asleep. Funnily enough, a friend of mine, who is also a writer (and one of the best I know), said the same thing.

I suspect I would have been an eager reader no matter the circumstances, but it didn’t hurt that my mother offered generous terms: £1 for every book completed. Perhaps this was the origin of a gimlet-eyed capitalist because I can tell you – I made a killing. (By which I mean probably a few hundred pounds, unfathomable wealth when translated into Beanie Babies.)

As I grew older, my tastes naturally changed. I went through a phase where I thought no prose could improve upon The Great Gatsby; another wherein I became obsessed with the Autobiography of Malcolm X. In college, I discovered Crime and Punishment, Critique of Pure Reason, The Passion According to G.H., Peter Singer’s moral philosophy, Rings of Saturn, and many others. I spent my sophomore summer obsessed with The Beat Generation, reading Kerouac and Burroughs and visiting a collection of Ginsburg’s private photographs several times over. (I eventually overdosed on Naked Lunch, the only book I both admired and hated.)

In the years after college, I devised mini curricula. I’d clump a group of books together around themes I wanted to explore (things like “inequality,” “memory,” or “lost love”) and work through them over a few months or more. Through this habit, I discovered authors like Leo Tolstoy, Maggie Nelson, Oliver Sacks, V.S. Naipaul, and Susan Sontag. 

I could keep writing another few thousand words on this topic, but I realize I have only half-answered your question. Books have been, since the beginning, a source of incredible pleasure, inspiration, and relief. I still consider it numinous that we can write a series of shapes on a page and provoke a range of rich responses: laughter and tears, bliss and fury, helplessness and determination. If you find the right words and put them in the right order, you can change people. Though many of the great dramas of the modern era are now told through television series, the novel has an unparalleled ability to replicate the depth of consciousness. No other medium can so reliably put you into someone else’s head and ask you to live there for a time. 

Here is a list of eleven books I love very much. Trying to reduce it to ten was too difficult. I can’t promise it is exhaustive or definitive – I am sure I must be forgetting something. 

  1. Disgrace by J.M. Coetzee. A book that takes place along a knife’s edge – and doesn’t slip. Disgrace is both the story of a wolfish professor handling personal failure and familial catastrophe, and an exploration of South Africa’s post-apartheid dilemmas. That the latter topic is investigated without judgment or moralizing is a testament to what is said and what isn’t; this is a story of ellipsis and absences. 
  2. Invisible Cities by Italo Calvino. I didn’t realize books were allowed to be like this. There is no plot. There are no stakes. There are barely any characters. And yet, it is a compelling, singularly imaginative read that asks you to deconstruct reality. While reading this book, I found myself staring at simple, everyday objects and systems – an office building, a subway line, a table – and reimagining them anew. 
  3. Autobiography of Red by Anne Carson. Though a mere 149 pages, Anne Carson’s prose poem about the mythological monster Geryon (rendered an abused child in this retelling) took me a surprisingly long time to read. That’s because nearly every sentence is a minor miracle. Take, for example, this charged moment between an older Geryon and love interest Herakles: “They were two superior eels / at the bottom of the tank and they recognized each other like italics.”
  4. Lolita by Vladimir Nabokov. “You can’t make every sentence do a backflip.” That was perhaps the single best writing advice I received, courtesy of a college fiction instructor. This is true – for everyone except Vladimir Nabokov. The Russian master is prose’s manic gymnast, vaulting across the page, spinning through sentences, and almost always sticking the landing. Pale Fire may be the most exaggerated example of this deranged gift, but Lolita is the more arresting, memorable narrative. 
  5. Norwegian Wood by Haruki Murakami. If I remember correctly, Norwegian Wood was written as the response to a challenge – at least in part. Though already a popular writer in his native Japan, there was a sense among literary critics that Murakami could only write the weird. Ask him to craft a love story, and the man would crumble into a litter of talking cats and dancing gnomes. Norwegian Wood put paid to such a theory. Not only is it a gorgeous, original love story, it remains heroically weird, albeit while staying within the confines of our reality. 
  6. Giovanni’s Room by James Baldwin. My favorite part of this tale of agony and shame and lost love arrives at the very end. Having lived in the immediate world of protagonist David and his charismatic paramour, Giovanni, Baldwin suddenly reminds us that everything we fear has already happened. The hope we have held onto; the pain we are holding back – both are pointless. It’s a delicately brutal maneuver, a kind of velvet garotte that reminds us of Baldwin’s remarkable poise and control.   
  7. The Golden Notebook by Doris Lessing. A mesmerizing, bamboozling book. Not so much as a sharp “descent into madness” as an invitation to a prolonged unraveling. Lessing welcomes the reader into the decaying mind of her protagonist and asks you to stay a while. In addition to being formally and stylistically brilliant, there’s a passage in which Lessing sends up Beat Generation writers like Kerouac with impressive fidelity and hilarious results. 
  8. The Sense of an Ending by Julian Barnes. If you put a gun to my head and asked me to pick the world’s best living writer, I would choose Barnes. Contemporaries Kazuo Ishiguro and Ian McEwan are better known internationally, but The Sense of an Ending author is every bit their equal. Perhaps Barnes is lesser known because his books tend to be miniatures, centering on the real tragedies that afflict small, ordinary lives. Flaubert’s Parrot is another of Barnes’ marvels. 
  9. On Chesil Beach by Ian McEwan. A pristine 166 pages. On Chesil Beach is a gorgeous, devastating portrait of a marriage – and a country. I could just have easily selected Atonement, another of McEwan’s masterpieces and perhaps the last book that left me genuinely devastated. But something about the precision of this novella has stayed with me. 
  10. Crime and Punishment by Fyodor Dostoevsky. A book of ideas that (mostly) doesn’t succumb to them. One does not have to spend any time considering the relative merits of strict utilitarianism or the philosophical deficiencies of an Übermensch to enjoy the tense cat-and-mouse game between murderer Raskolnikov and police chief Porfiry or Dostoevsky’s lustrous depiction of madness. The ending is, however, a disappointment. 
  11. Close Range by Annie Proulx. There’s a passage in “The Mud Below,” the second story in this collection, that reminds you that heartache is a gift for the living, a privilege, an immaculate, mortal pain. In truth, the entire compilation is an understated ode to grief, including its most famous story, “Brokeback Mountain.” Another of Proulx’s books, The Shipping News, is well worth reading, featuring a male protagonist unlike any I’ve found elsewhere.

(Ah, I knew I would miss someone. George Saunders, saved for another time.)  

6. Have you encountered any challenges or obstacles in creating and managing your newsletter, and if so, how have you addressed them? Samyak, Humming.World

Yes, many! An appraisal of challenges we’ve faced – and our approaches to overcoming them – are most fully discussed in The Generalist’s one-year and two-year recaps. There’s a lot of tactical information, including the tools we’ve used, strategies we’ve deployed, and lessons we’ve learned. 

The biggest challenge I’ve faced is managing my energy and emotional reserves. Writing The Generalist every week is very fun. It is also frequently stressful and tiring. Maintaining a quality bar I’m happy with week after week, month after month, can take a toll, especially if you don’t build in time to decompress. I haven’t burned out yet, but I have gotten close occasionally.

To be honest, I don’t have a great solution just yet. I hope that new challenges activate new reserves of energy; that hiring another writer will elevate my game and reduce the reliance on me; and that I might learn to be stricter in forcing myself to recharge. (It is always tiresome to have someone say, seriously, that they “just need to learn to relax,” but here we are.) I also think I need to make more time to write fiction, which I find restorative and immensely pleasurable. 

7. What’s your proxy to say if you are living a life that you find meaningful? – A Curious Fox

Not long ago, a college classmate reminded me how I answered a version of this question at graduation. I said I wanted to live “an original life.” At the time, I suspect that was a reaction to the feeling that I spent my late-teenage years and early twenties engaged in productive orthodoxy: succeeding academically, taking up careerist hobbies, and competing for impressive-sounding internships. 

On something of a whim, I decided to study abroad in Nepal during my junior year and were it not for the intense solitude and self-reflection that trip forced, I probably would have pummeled my way through three miserable years of law school and an even more miserable stint as an associate before crashing into a quarter-life crisis.

To me, a meaningful life is one that authentically, originally coincides with one’s particular skills, passions, and temperament. 

For whatever reason, I react poorly to environments that force me to lop off a part of myself, shave down locally undesirable edges, and follow a vision that does not match my own. This is dramatic language – and I suspect others experience such environments differently – but it is how I feel. At least in my adult life, I have only found meaning when chasing a problem of my own definition.

The Generalist’s work is provided for informational purposes only and should not be construed as legal, business, investment, or tax advice. You should always do your own research and consult advisors on these subjects. Our work may feature entities in which Generalist Capital, LLC or the author has invested.